Hydrochloric Acid → HCID 21974587, compound

HRID 31115Notes

Reaction equation

HRID 31115 reaction equation
C(N[NH:5][C:6]1(C(OCC)=O)[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:16][CH3:17])[NH:8][C:7]1=[O:18])(=O)C.[ClH:24]>>[ClH:24].[NH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:16][CH3:17])[NH:8][C:7]1=[O:18]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 219745923-Acetamidoamino-3-carboethoxy-5-methoxy-3,4-dihydrocarbostyril

Product 1

HCID 21974587HCID 21974587, compound

Procedure

A mixture of 3-acetamidoamino-3-carboethoxy-5-methoxy-3,4-dihydrocarbostyril (5.7 g) and 6 M aqueous hydrochloric acid (75 mL) was refluxed for 6 h. This mixture was evaporated to a solid which was triturated with acetonitrile. Filtration provided 3-amino-5-methoxy-3,4-dihydrocarbostyril hydrochloride (3.8 g, mp 301-302° C. with decomp.) as gray crystals. The free base, 3-amino-5-methoxy-3,4-dihydrocarbostyril, was prepared by ion exchange on an SCX column (United Chemical Technologies, CLEAN-UP Extraction Column, sorbent CUBCX1HL, Synthesis 1997, 553-558) by loading in methanol and eluting with methanol, followed by 2 M methanolic ammonia. The ammonia containing eluant was evaporated to provide 3-amino-5-methoxy-3,4-dihydrocarbostyril.

Workup

  1. temperaturewas refluxed for 6 h
  2. customThis mixture was evaporated to a solid which
  3. customwas triturated with acetonitrile
  4. filtrationFiltration

Sources & evidence

ORD record
ord-41a06aaa5f8945be9b2d8eaffb31f1f8
Source dataset
uspto-grants-2008_09
Patent number
US07425550B2

Reaction notes

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